Copending U.S. patent application Ser. No. 687,318, filed May 26, 1976 by Elena M. Bingham and William Joseph Middleton, which is a continuation-in-part of U.S. patent application Ser. No. 597,502, filed July 21, 1975, now abandoned, discloses certain novel 3-fluorobenzodiazepines of the formula: ##STR1## where X is Cl, Br, NO.sub.2, or CF.sub.3 ;
Y is H, Cl, Br or F;
D is H, hydrocarbyl of 1-4 carbons, --CH.sub.2 CF.sub.3, --CONHR, --CH.sub.2 CH.sub.2 NR.sub.2, or --CH.sub.2 CH.sub.2 NR.sub.2.A, where R is alkyl of 1-4 carbons and A is a pharmaceutically suitable acid; PA1 B is O; or PA1 B and D together is .dbd.N--N.dbd.C(R')-- where R' is H or C.sub.1 -C.sub.4 alkyl, PA1 Y is H, Cl, Br or F; and PA1 Z.sup.1 and Z.sup.2 are Cl or Br. PA1 Y is H, Cl, Br or F; and PA1 Z is I, Br, CF.sub.3 SO.sub.2 O--, FSO.sub.2 O--, CCl.sub.3 SO.sub.2 O-- or CH.sub.3 OSO.sub.2 O--.
and the use of such compounds as tranquilizers, muscle relaxants and sedatives in mammals. In addition, Bingham and Middleton disclose a process for making such compounds by reaction of the corresponding 3-hydroxybenzodiazepine with a dialkylaminosulfur trifluoride as follows: ##STR2## where R.sup.3 and R.sup.4 are a primary alkyl group of 1-4 carbons or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5.
Copending U.S. patent application Ser. No. 807,075, filed on June 16, 1977 by William Joseph Middleton, now U.S. Pat. No. 4,182,760, discloses an improved process for preparing such 3-fluorobenzodiazepines, which improved process can be summarized schematically by the following equations: ##STR3## where X is Cl, Br, NO.sub.2 or CF.sub.3 ;
Middleton also discloses that starting material (1) can be prepared by the process disclosed in U.S. Pat. No. 3,398,139.
In addition, copending U.S. patent application Ser. No. 807,074, filed June 16, 1977 by Elena M. Bingham and Arthur J. Elliott, now U.S. Pat. No. 4,160,092, discloses an improved process for preparing the N-methylaminobenzophenone anti-oxime used as the starting material in Middleton's improved process discussed immediately above. The Bingham and Elliott process can be summarized schematically by the following equations: ##STR4## where X is Cl, Br, NO.sub.2 or CF.sub.3 ;
Bingham and Elliott also disclose that the starting material quinazolinone 3-oxides can be prepared by a process taught by Sulkowski and Childress, J. Org. Chem., 27, 4424 (1962).